Para-aminoacetyl meta-toluidin.



UNITED STATES PATENT OFFICE.

(KARL llElUENltElCH, ()l VOHWINKEL, NEAR ELBERFELD, GERMANY, ASSIGNOR TOFAR- BENFABRIKEN VUltM. Fltllflblt. BAYER dz 00.,

OF ELBERF-ELD, GERMANY, A ()ORPORA- PARA'AMINOACETYL META-TOLUIDIN.

To all whom it may concern:

Be it known that I, CARI. IlnInaNREIen, doctor of; philosophy, chemist,citizen of the German Empire, residing at Vohwinkel, near Elhcrield,(vlcrmany, Kingdom of Prussia, have invented new and useful Improvementsin Para-A minoaectyl Meta-'loluidin, of which the following is aspecification.

My invention relates to the production of the hitherto unknownacidylamino-toluidius having the formula:

(it meaning an acidyl radiele) which are valuable intermediate compoundsfor the manufacture of dyestuffs.

The process for producing these compounds consists in first combiningdiazol cnzone with meta-toluidin to )roducc benzeneazo-mcta-toluidin,seeondiy treating this compound with aeidylizing agents, such as aorticanhydrid, hcnzoyl chlorid ctc., and finally treating the acidylizedbenzene-anometa-toluidins of the formula:

with reducing agents.

The new n'oduots are crystalline compounds soluble in water and easilysoluhlc in alcohol, toluylemliamin (Cll :Nll :Nll =1:3:ti) lacing formedby heating them with caustic :tlkalics.

ln order to carry out my new proccss I can 4'. y. procccd as follows,the parts living hy \rcight'. .13; parts of aniliu arc dhizotizcd in theusual manner by means ol sodium nitrite and h \'drochlorlc acid and totho diamcompouml 15 parts ol' uwta-toluidin arc added. When the reactionis eomplcto the mixtul'c is rcmh-rcd' alkaline by addition of causticsoda l and thc excess of meta-toluidin is dl'ivcn oll' with steam.Attcrcmiling thc dycstull' solidilics. ll is then hcatcd to from .N) tollltl and mixcd with ll parts ol acetic. anhydrid whilc stirring. Therear- Specification of Letters Patent.

Application filed. March 10, 1908.

Patented Oct. 27, 1908.

Serial No. 420,249. (Specimens.)

tion mass solidifies during cooling. It ispulverized and slowly stirredinto a boiling mixture of 30 parts of iron filings with. parts of water.The reaetion begins at once -and is terminated by further boiling themixture while stirring for 2 hours. \Vhen all the azo compound hasdisappeared, steam is passed into the hot liquid, upon which anilinpasses over.

The reunuumg liquid is rendered alkaline by the addition of sodiumoarhonate and is separated from the iron by filtration. The newpara-mninoaeet-metatoluidin is isolated by addition of common salt tothe filtrate. lt crystallizes from hot water in the shape of whitishcrystals melt ing at 71 0., soluble in water, alcohol, ether andbenzene. Amiuo-meta-toluidin is formed by heating it with causticalkalies.

The formation of the new para-aniinoaeetmeta-toluidin taltcs'placoprobably aecord x" ing to the following equations:

Correction in Letters Patent No. 902,150.

which compounds are crystalline pow'ders soluble in Water and easilsoluble in alcohol; aminotoluidin (CH zN :NH,= 1 :3 :6) be in formed byheating them with caustic a1 alies, substantially as described.

2. The herein-described new aminoaoetyltoluidin of the formula;

CH ck \/\NH.C0CH3, which is a whitish crystalline powder melting [SEAL]my hand in the presence of two subscribing Witnesses.

min, inimn'imiou, [In s] Witnesses:

O'r'ro KONIG, Heme Vmnorr.

It is hereby certified that in Letters Patent No. 902,150, grantedOctober 27, 1908,

upon the application of Carl Heidenreich, of Vohwinkel, near Elberfeld,Germany, for

- an improvement in Para-Aminoacetyl Meta-Toluidin, an error appears inthe printed specification requiring correction, as follows: In line 78,page 1, the formula (lH N NiCl :shou1dread c reer: N. 01

-ters Patent should be read with this correction therein that the samemay conform to the record of the case in the Patent Office.

; and that the said Let- Signed and sealed this 17th day of November, A.D., 1908.

C. O. BILLINGS,

Acting Commissioner of Patents.

Correction in Letters Patent No. 902,150.

which compounds are crystalline pow'ders soluble in Water and easilsoluble in alcohol; aminotoluidin (CH zN :NH,= 1 :3 :6) be in formed byheating them with caustic a1 alies, substantially as described.

2. The herein-described new aminoaoetyltoluidin of the formula;

CH ck \/\NH.C0CH3, which is a whitish crystalline powder melting [SEAL]my hand in the presence of two subscribing Witnesses.

min, inimn'imiou, [In s] Witnesses:

O'r'ro KONIG, Heme Vmnorr.

It is hereby certified that in Letters Patent No. 902,150, grantedOctober 27, 1908,

upon the application of Carl Heidenreich, of Vohwinkel, near Elberfeld,Germany, for

- an improvement in Para-Aminoacetyl Meta-Toluidin, an error appears inthe printed specification requiring correction, as follows: In line 78,page 1, the formula (lH N NiCl :shou1dread c reer: N. 01

-ters Patent should be read with this correction therein that the samemay conform to the record of the case in the Patent Office.

; and that the said Let- Signed and sealed this 17th day of November, A.D., 1908.

C. O. BILLINGS,

Acting Commissioner of Patents.

It is hereby certified that in Letters Patent N 0. 902,150, grantedOctober 27, 1908, upon the application of Carl Heidenreich, ofVohwinkel, near Eiberfeld, Germany, for an improvement inPara-Aminoacetyi Meta-Toluidin, an error appears in the printedspecification requiring correction, as follows: In line 78, page 1, theformula CH N N C1 should read C H N N. C1 and that the said Let- -tersPatent should be read with this correction therein that the same mayconform to Correction in Letters Patent No. 902,150.

the record of the case in the Patent Ofiice.

Signed and sealed this 17th day of November, A. D., 1908.

[SEAL] (l O. BILLINGS,

A ct'ing Commissioner of Patents.

